Homes with a Private Pool

Stay in style with a private pool on Hilton Head Island. While vacationing on Hilton Head, there’s nothing more relaxing than enjoying the pool with your friends and family. Our Hilton Head vacation rentals with private pools give you a place to dive into a refreshing afternoon. Located in Hilton Head’s best neighborhoods, with great access to beaches, golf courses, and family entertainment, these special vacation homes are perfect for families and groups. Book your Hilton Head poolside vacation today!


Properties Available 177 properties available
Walk to the Atlantic Ocean and Coligny Plaza for dining and shopping... what more do you need!?? There are three (3) bedrooms and two (2) full bathrooms, offering sleeping arrangements for up to seven. Updated furnishings complete the look of this home, providing a "shore to please" vacation. Complete with a backyard oasis, including a private pool
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

1 Bittern Street
House
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
West Garrison is located in a quiet neighborhood within Sea Pines Resort The main level of the house has a large living and dining area to accommodate all family gatherings. There is a second living area on the main level that is perfect for watching TV. Both living areas have a queen sleeper sofa. The main level showcases a master bedroom with an
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

1 West Garrison
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests
Rating 5 (3)
Your very own private retreat in the heart of Sea Pines! This 3-bed, 3-bath single-level home offers an open concept with multiple living spaces for the entire family. The Tommy Bahama décor throughout and Brazilian cherry wood floors are highlighted by the numerous skylights which allow an abundance of natural light in. Upon entering, you will fin
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

12 Deer Run Lane
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (2)
128 Dune is just steps away from the glimmering Atlantic Ocean! This 3 bedroom, 3.5 bath home with private *heated pool has a prime location in North Forest Beach. Beautiful hardwood flooring in the living room, quartz counter tops in the kitchen, and coastal chic furniture are just a few of the upgrades. The bathrooms have been completely redesign
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

128 Dune Lane
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 6 guests
Rating 5 (4)
Only steps away from the ocean, this home is bright and spacious with beautiful beach decor. The first floor offers an open living room and kitchen with large windows and high ceilings. There is a separate dining room, as well as bar seating and a card/breakfast table. A king bedroom and full hall bath and powder room are also on this floor. The up
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

15 Ibis St
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Welcome to this beautiful ranch-style beach house, just perfect for your next getaway! Complete with a backyard oasis, including a private pool and screened-in porch... it\'s perfect for your island escape. There are three (3) bedrooms and two (2) full bathrooms, offering sleeping arrangements for eight. The furnishings complete the look of this ho
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

15 Pelican
House
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (5)
Overlooking the 10th tee of Harbour Town Golf Links, this home is beautifully decorated and features 3-beds and 3.5-baths. Take a short stroll to the Sea Pines Racquet Club, the Harbour Town Clubhouse, and the Harbour Town Yacht Basin. Stay in and enjoy the poolside views of the golf course from the living room, private den, and two of the master s
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

21 Windjammer Court
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 8 guests
Rating 5 (3)
This oceanfront home features 3 bedrooms and 2 bathrooms to sleep up to 10 guests comfortably and is located in the quiet area of Folly Field, one of Hilton Head\'s finest beaches! As you walk into the great room of the home, you are welcomed by a newly updated kitchen, dining area, and living room! Numerous windows allow plenty of natural light to
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

22 Sand Dollar
House
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 10 guests
Rating 5 (1)
This 3-bed, 3-bath traditional Sea Pines beach home with a private pool is just 3rd row from the ocean! This ranch-style home has a large open kitchen and Corian countertops. The kitchen area encompasses a nice dining area and glassed-in Carolina room. Nearby to the Carolina room is a spacious living room that looks over the pool. Sliding doors
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

22 Surf Scoter
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 4 (1)
This charming 3-bed, 3-bath vacation home is located in the South Beach area of Sea Pines. *Heated private pool, spa, and just a short walk to the beach; this house is perfect for families or small groups. Also close by are all the activities offered by the South Beach Marina including charter fishing, water sports, shopping, entertainment, and of
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

3 Scaup Court
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (5)
This 2nd row, a low country style beach house in Palmetto Dunes Plantation is built to make vacation dreams come true. This home had a full kitchen renovation completed January 2023. Wide wrap-around porches and updated Carolina room provide a comfortable place to enjoy ocean breezes morning, noon, and night! Whether on the deck peering out to the
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

4 Iron Clad
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests
Rating 5 (7)
This tastefully renovated 3-bedroom, 3-bath home with a private heated pool! It is a 5-minute walk to the beach! Located in the beautiful Sea Pines Plantation, it is a quick stroll to the South Beach Marina Village with shopping, restaurants, and nightly entertainment. This charming one-level home boasts an open floor plan with a kitchen overloo
sand-dollar Special
15 Percent Off All Villas And Homes

Fall in LOVE with Hilton Head Island!

Get cozy with 15% off homes and villas this winter season with a variety of properties to choose from. Sea Pines, Shipyard, Palmetto Dunes, or Forest Beach? The options are endless!

XOXO,

The Vacation Company

*Minimum stay of 4 nights

4 Merganser Court
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 4.9 (18)

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